CN1129582C - 作为钾通道调节剂的3－取代－4－芳基喹啉－2－酮衍生物 - Google Patents
作为钾通道调节剂的3－取代－4－芳基喹啉－2－酮衍生物 Download PDFInfo
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- CN1129582C CN1129582C CN99813902A CN99813902A CN1129582C CN 1129582 C CN1129582 C CN 1129582C CN 99813902 A CN99813902 A CN 99813902A CN 99813902 A CN99813902 A CN 99813902A CN 1129582 C CN1129582 C CN 1129582C
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- Prior art keywords
- trifluoromethyl
- chloro
- quinolinone
- phenyl
- hydroxy phenyl
- Prior art date
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- 102000004257 Potassium Channel Human genes 0.000 title abstract description 13
- 108020001213 potassium channel Proteins 0.000 title abstract description 13
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 17
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 102000005702 Calcium-Activated Potassium Channels Human genes 0.000 claims abstract 2
- 108010045489 Calcium-Activated Potassium Channels Proteins 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 125
- 239000000203 mixture Substances 0.000 claims description 42
- -1 methoxyl group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 230000005611 electricity Effects 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
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- QESHSZWKJULSAR-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-(2-hydroxyethyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)C(CCO)=C1C1=CC(Cl)=CC=C1O QESHSZWKJULSAR-UHFFFAOYSA-N 0.000 claims description 6
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- XNJYCAFGCFALEG-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-(3-hydroxypropyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)C(CCCO)=C1C1=CC(Cl)=CC=C1O XNJYCAFGCFALEG-UHFFFAOYSA-N 0.000 claims description 4
- QUKGHUWTRXCPOA-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-(4-hydroxyphenyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C1=CC(O)=CC=C1C(C(NC1=CC=C(C=C11)C(F)(F)F)=O)=C1C1=CC(Cl)=CC=C1O QUKGHUWTRXCPOA-UHFFFAOYSA-N 0.000 claims description 4
- FJXQSZCNFZVKCJ-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-(hydroxymethyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)C(CO)=C1C1=CC(Cl)=CC=C1O FJXQSZCNFZVKCJ-UHFFFAOYSA-N 0.000 claims description 4
- GIOMDNTVTJLPLS-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C1=CC(O)=CC=C1CC(C(NC1=CC=C(C=C11)C(F)(F)F)=O)=C1C1=CC(Cl)=CC=C1O GIOMDNTVTJLPLS-UHFFFAOYSA-N 0.000 claims description 4
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
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- VXOZJABAXSOTPK-UHFFFAOYSA-N 3-(4-aminophenyl)-4-(5-chloro-2-hydroxyphenyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C1=CC(N)=CC=C1C(C(NC1=CC=C(C=C11)C(F)(F)F)=O)=C1C1=CC(Cl)=CC=C1O VXOZJABAXSOTPK-UHFFFAOYSA-N 0.000 claims description 3
- JETCKZALJDZAMQ-XFFZJAGNSA-N 4-(5-chloro-2-hydroxyphenyl)-3-[(z)-2-fluoro-3-hydroxyprop-1-enyl]-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)C(/C=C(F)/CO)=C1C1=CC(Cl)=CC=C1O JETCKZALJDZAMQ-XFFZJAGNSA-N 0.000 claims description 3
- KPARSOZCXRNLDV-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-[2-(4-hydroxyphenyl)ethyl]-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C1=CC(O)=CC=C1CCC(C(NC1=CC=C(C=C11)C(F)(F)F)=O)=C1C1=CC(Cl)=CC=C1O KPARSOZCXRNLDV-UHFFFAOYSA-N 0.000 claims description 3
- ABBYLWIDZCVZRN-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-methyl-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)C(C)=C1C1=CC(Cl)=CC=C1O ABBYLWIDZCVZRN-UHFFFAOYSA-N 0.000 claims description 3
- HADKCEVOIBBFSA-UHFFFAOYSA-N n-[4-[4-(5-chloro-2-hydroxyphenyl)-2-oxo-6-(trifluoromethyl)-1h-quinolin-3-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(C(NC1=CC=C(C=C11)C(F)(F)F)=O)=C1C1=CC(Cl)=CC=C1O HADKCEVOIBBFSA-UHFFFAOYSA-N 0.000 claims description 3
- JETCKZALJDZAMQ-YRNVUSSQSA-N 4-(5-chloro-2-hydroxyphenyl)-3-[(e)-2-fluoro-3-hydroxyprop-1-enyl]-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)C(\C=C(F)/CO)=C1C1=CC(Cl)=CC=C1O JETCKZALJDZAMQ-YRNVUSSQSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 claims 3
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 89
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- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
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- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Reproductive Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Gynecology & Obstetrics (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Pregnancy & Childbirth (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11107998P | 1998-12-04 | 1998-12-04 | |
| US60/111,079 | 1998-12-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1329599A CN1329599A (zh) | 2002-01-02 |
| CN1129582C true CN1129582C (zh) | 2003-12-03 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN99813902A Expired - Fee Related CN1129582C (zh) | 1998-12-04 | 1999-12-01 | 作为钾通道调节剂的3－取代－4－芳基喹啉－2－酮衍生物 |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US6184231B1 (ru) |
| EP (1) | EP1133474B1 (ru) |
| JP (1) | JP2002531549A (ru) |
| KR (1) | KR100641254B1 (ru) |
| CN (1) | CN1129582C (ru) |
| AR (1) | AR021867A1 (ru) |
| AT (1) | ATE354569T1 (ru) |
| AU (1) | AU755202B2 (ru) |
| BR (1) | BR9915744A (ru) |
| CO (1) | CO5150159A1 (ru) |
| CZ (1) | CZ20011965A3 (ru) |
| DE (1) | DE69935245T2 (ru) |
| DK (1) | DK1133474T3 (ru) |
| ES (1) | ES2281975T3 (ru) |
| HU (1) | HUP0201613A3 (ru) |
| ID (1) | ID28959A (ru) |
| IL (1) | IL142457A (ru) |
| MY (1) | MY115935A (ru) |
| NO (1) | NO318897B1 (ru) |
| NZ (1) | NZ510987A (ru) |
| PE (1) | PE20001327A1 (ru) |
| PL (1) | PL196955B1 (ru) |
| PT (1) | PT1133474E (ru) |
| RU (1) | RU2240998C2 (ru) |
| TR (1) | TR200101339T2 (ru) |
| TW (1) | TW495504B (ru) |
| WO (1) | WO2000034244A1 (ru) |
| ZA (1) | ZA200104455B (ru) |
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| EP1198456B1 (en) * | 1999-08-03 | 2007-09-19 | Abbott Laboratories | Potassium channel openers |
| US6436944B1 (en) * | 1999-09-30 | 2002-08-20 | Pfizer Inc. | Combination effective for the treatment of impotence |
| TW562799B (en) * | 1999-12-01 | 2003-11-21 | Bristol Myers Squibb Co | Preparation of 3-substituted-4-arylquinolin-2-one derivatives |
| AU2002213204A1 (en) * | 2000-10-13 | 2002-04-22 | Bristol-Myers Squibb Company | Selective maxi-K- potassium channel openers functional under conditions of high intracellular calcium concentration, methods and uses thereof |
| US6831102B2 (en) * | 2001-12-07 | 2004-12-14 | Bristol-Myers Squibb Company | Phenyl naphthol ligands for thyroid hormone receptor |
| WO2003051878A1 (en) * | 2001-12-14 | 2003-06-26 | Merck Frosst Canada & Co. | Quinolinones as prostaglandin receptor ligands |
| AU2003225305A1 (en) | 2002-05-08 | 2003-11-11 | Bristol-Myers Squibb Company | Pyridine-based thyroid receptor ligands |
| US7405234B2 (en) * | 2002-05-17 | 2008-07-29 | Bristol-Myers Squibb Company | Bicyclic modulators of androgen receptor function |
| MY139563A (en) | 2002-09-04 | 2009-10-30 | Bristol Myers Squibb Co | Heterocyclic aromatic compounds useful as growth hormone secretagogues |
| US7632858B2 (en) * | 2002-11-15 | 2009-12-15 | Bristol-Myers Squibb Company | Open chain prolyl urea-related modulators of androgen receptor function |
| US6939968B2 (en) * | 2002-12-23 | 2005-09-06 | Bristol-Myers Squibb Company | Atropisomers of 3-substituted-4-arylquinolin-2-one derivatives |
| TW200504021A (en) * | 2003-01-24 | 2005-02-01 | Bristol Myers Squibb Co | Substituted anilide ligands for the thyroid receptor |
| WO2004066929A2 (en) * | 2003-01-24 | 2004-08-12 | Bristol-Myers Squibb Company | Cycloalkyl containing anilide ligands for the thyroid receptor |
| ATE479667T1 (de) | 2003-02-06 | 2010-09-15 | Bristol Myers Squibb Co | Als kinaseinhibitoren geeignete verbindungen auf thiazolylbasis |
| US7557143B2 (en) | 2003-04-18 | 2009-07-07 | Bristol-Myers Squibb Company | Thyroid receptor ligands |
| PT1618092E (pt) | 2003-05-01 | 2010-11-22 | Bristol Myers Squibb Co | Compostos de pirazol-amida substituídos com arilo úteis enquanto inibidores de cinase |
| EP1644335A4 (en) | 2003-07-11 | 2008-06-04 | Bristol Myers Squibb Co | TETRAHYDROQUINOLINE DERIVATIVES COMPRISING MODULATORS OF CANNABINOID RECEPTORS |
| US7326788B2 (en) | 2003-07-22 | 2008-02-05 | Janssen Pharmaceutica N.V. | Quinolinone derivatives as inhibitors of c-fms kinase |
| JP4722851B2 (ja) * | 2003-09-23 | 2011-07-13 | メルク・シャープ・エンド・ドーム・コーポレイション | キノリンカリウムチャネル阻害剤 |
| US7825131B2 (en) | 2003-09-23 | 2010-11-02 | Merck Sharp & Dohme Corp. | Quinoline potassium channel inhibitors |
| WO2005037199A2 (en) | 2003-10-10 | 2005-04-28 | Bristol-Myers Squibb Company | Pyrazole derivatives as cannabinoid receptor modulators |
| US7179920B2 (en) * | 2003-10-14 | 2007-02-20 | Bristol-Myers Squibb Company | 3-thia-4-arylquinolin-2-one derivatives |
| US7132542B2 (en) | 2003-10-14 | 2006-11-07 | Bristol-Myers Squibb Company | Compounds for the treatment of male erectile dysfunction |
| US7145013B2 (en) * | 2003-10-14 | 2006-12-05 | Bristol-Myers Squibb Company | 3-thia-4-arylquinolin-2-one derivatives |
| US7002015B2 (en) * | 2003-10-14 | 2006-02-21 | Bristol-Myers Squibb Company | 3-Thia-4-arylquinolin-2-one derivatives as smooth muscle relaxants |
| US7049309B2 (en) * | 2003-10-14 | 2006-05-23 | Bristol-Myers Squibb Company | 3-Thia-4-arylquinolin-2-one potassium channel modulators |
| US7151180B2 (en) * | 2003-10-14 | 2006-12-19 | Bristol-Myers Squibb Company | Potassium channel modulators |
| US20070060629A1 (en) * | 2003-10-17 | 2007-03-15 | Yasuhiro Imanishi | Large conductance calcium-activated k channel opener |
| KR101167573B1 (ko) * | 2003-11-07 | 2012-07-30 | 노바티스 백신즈 앤드 다이아그노스틱스 인코포레이티드 | 개선된 약학적 성질을 갖는 퀴놀리논 화합물의 약학적으로허용가능한 염 |
| US7256208B2 (en) * | 2003-11-13 | 2007-08-14 | Bristol-Myers Squibb Company | Monocyclic N-Aryl hydantoin modulators of androgen receptor function |
| US7820702B2 (en) * | 2004-02-04 | 2010-10-26 | Bristol-Myers Squibb Company | Sulfonylpyrrolidine modulators of androgen receptor function and method |
| US20050182105A1 (en) * | 2004-02-04 | 2005-08-18 | Nirschl Alexandra A. | Method of using 3-cyano-4-arylpyridine derivatives as modulators of androgen receptor function |
| US7378426B2 (en) | 2004-03-01 | 2008-05-27 | Bristol-Myers Squibb Company | Fused heterotricyclic compounds as inhibitors of 17β-hydroxysteroid dehydrogenase 3 |
| US7388027B2 (en) * | 2004-03-04 | 2008-06-17 | Bristol-Myers Squibb Company | Bicyclic compounds as modulators of androgen receptor function and method |
| US7696241B2 (en) * | 2004-03-04 | 2010-04-13 | Bristol-Myers Squibb Company | Bicyclic compounds as modulators of androgen receptor function and method |
| US7625923B2 (en) | 2004-03-04 | 2009-12-01 | Bristol-Myers Squibb Company | Bicyclic modulators of androgen receptor function |
| US7253167B2 (en) * | 2004-06-30 | 2007-08-07 | Bristol-Myers Squibb Company | Tricyclic-heteroaryl compounds useful as kinase inhibitors |
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| EP1676573A1 (en) * | 2004-12-30 | 2006-07-05 | Laboratorios Del Dr. Esteve, S.A. | Phamaceutical composition comprising a 2,5-dihydroxybenzenesulfonic-compound, a potassium ion channel modulator and a phosphodiesterase type 5 inhibitor |
| WO2006076598A2 (en) * | 2005-01-12 | 2006-07-20 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoid receptor modulators |
| WO2006076568A2 (en) | 2005-01-12 | 2006-07-20 | Bristol-Myers Squibb Company | Thiazolopyridines as cannabinoid receptor modulators |
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| US20060178388A1 (en) * | 2005-02-04 | 2006-08-10 | Wrobleski Stephen T | Phenyl-substituted pyrimidine compounds useful as kinase inhibitors |
| WO2006086464A2 (en) * | 2005-02-10 | 2006-08-17 | Bristol-Myers Squibb Company | Dihydroquinazolinones as 5ht modulators |
| AU2006216629A1 (en) * | 2005-02-24 | 2006-08-31 | Janssen Pharmaceutica N.V. | Novel quinoline derivatives as potassium ion channel openers |
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| US7317012B2 (en) * | 2005-06-17 | 2008-01-08 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoind-1 receptor modulators |
| US20060287342A1 (en) * | 2005-06-17 | 2006-12-21 | Mikkilineni Amarendra B | Triazolopyrimidine heterocycles as cannabinoid receptor modulators |
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